Anthelmintic bis-thioureido benzene derivative

ABSTRACT

This invention relates to the control of internal parasites. More specifically, this invention relates to the use of anthelmintic active compounds defined by the following formula:   WHEREIN R can be hydrogen, nitro, halogen or lower alkyl group and R1 is a lower alkyl group.

United States Patent [19] Menu [451 May 14,1974

[ ANTHELMINTIC BIS-THIOUREIDO BENZENE DERIVATIVE [75.] Inventor: Julius Joel Menn, Saratoga, Calif.

[73] Assignee: Stauffer Chemical Company, New

York, NY.

[22] Filed: Sept. 2, 1971 [21] App]. No.: 177,471

OTHER PUBLICATIONS Chemical Abstracts, Vol. 71 (1969), p. 70347h Primary ExaminerVincent D. Turner Attorney, Agent, or Firm-Daniel C. Block [57] ABSTRACT This invention relates to thecontrol of internal parasites. More specifically, this invention relates to the use of anthelmintic active compounds defined by the ,felwleeiq m le vvherein R can be hydrogen, nitro, halogen or lower alkyl group and R is a lower alkyl group.

1 Claim, No Drawings ANTHELMINTIC BIS-THIOUREIDO BENZENE DERIVATIVE DESCRIPTION OF THE INVENTION It has been discovered that certain bis-thioureido benzene compounds possess high anthelmintic activity. The compounds of this invention correspond to the following formula:

wherein R can be selected from the group consisting of hydrogen, nitro, halogen, or lower alkyl and R is a lower alkyl group.

A 50 percent wettable powder of l,2-bis[(3-ethoxycarbonyl)thioureido] benzene was made up with water and dosed orally, by drenching bottle, to sheep,

a day after treatment and mixed with water so that samples could be taken for estimation of the numbers of small worms expelled, and the whole output sieved for large species.

Three days post-dosing the sheep were killed and the worms left in the intestinal tract counted by the usual methods, i.e. dilution counts for the smaller worms and direct sieve counts for the larger ones. The results are tabulated in Table I.

TABLE I Worms Worms Worms Worms Genus Expelled Retained Expelled Expelled Retained Expelled osprtagla l() 0 lOO NOT TESTED Trichostrongylus 50 0 m0 Chabertia l 0 l 00 d-o. Oesophagostomum Venulosum NOT NOT TESTED v TESTED Nematodirus d0. NOT TESTED Haemonchus NOT 100% Effective TESTED 40 20 Worlrrscl Worms Worms Worms EX 6 e Retained Ex elled Ex elled Retained Ex elled 08361138181 loo i) 200* l Tn h lr y 1500 3 98 1300 n [00 Chabertia 112 0 100 89 2. 98 Oesophagostomum Venulosum 24 5 83 79 16 83 Nematodirus NOT 200 0 100 I TESTED Haemonchus NOT lNEFFECTlVE H. TESTED The manner of synthesizing the compounds of this 40 invention are described in the prior art. They are also described as having fungicidal activity. However, the use of the compounds to control internal parasites is not known or described in the prior art.

The compounds of this invention can be administered to the habitat of the parasites to be controlled in any convenient manner, such as wettable preparations, aqueous solutions, emulsions, powdery preparations and the like, in combination with diluents such as diatomaceous earth, kaolin, clay, talc, vegetable or mineral oils and the like. The amount of active compound administered will of course vary depending on the species of parasite sought to be controlled.

In order to illustrate the merits of the present invention, the following evaluation tests were conducted.

is ethyl.

wherein Ris hydrogen and R Disclaimer i 3,810,992.Julius J oeZ Men-n, Saratoga, Calif. ANTHELMIN TIC BIS- 1 THIOUREIDO BENZENE DERIVATIVE. Patent dated May 14, i 1974. Disclaimer filed Nov. 1, 1976, by the assignee, Stew/fie? Chemz'oal Oompany. Hereby enters this disclaimer to claim 1 of said patent.

[Ofiicz'al Gazette August 16, 1977.]

Notice of Adverse Decision in Interference In Interference No. 99,307, involving Patent No. 3,810,992, J. J. Menn, ANTHELMINTIC BIS-THIOUREIDO BENZENE DERIVATIVE, final judgment adverse to the patentee was rendered Nov. 15, 1976, as to claim 1.

[Ofiicial Gazette March 22, 1.977.]

Po-ww UNITED STATES PATEL T OFFICE CERTIFICATE OF CORRECTION Pstent No. "3,810,992 Dated May 14, 1974 Inventor(s) ilulius J. Menn It is certified that error appears in the above-identified patent and that said Letters; Patent are hereby corrected as shown below:

.Under the heading "Table I" please insert 'the sub-heading ---mg/kg of Body Weight--; over the first set of three columns entitled "Worms Expelled", "Worms Retained" and "7, Expelled" insert the numeral ---6O---; and over the second set of three columns entitled "Worms Expelled", "Worms Retained" and "'7, Expelled" insert the numeral --50--.

i In Column 2, line 55, omit the line reading "wherein R is hydrogen and R is ethyl."

Signed and sealed this 1st day of October 1974.

(SEAL) Attest:

C. MARSHALL DANN Commissioner of Patents MCCOY M. GIBSON JR. Attesting Officer 

